Carbohydrate-Based Spiro-1,3-oxazolidine-2-thiones:
Stereoselective Approaches Using Aziridines and Epoxides

Sébastien Tardy; Joana Lobo Vicente; Arnaud Tatibouët; Gilles Dujardin; Patrick Rollin

doi:10.1055/s-2008-1067266

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Synthesis 2008(19): 3108-3120
DOI: 10.1055/s-2008-1067266

PAPER

Carbohydrate-Based Spiro-1,3-oxazolidine-2-thiones: Stereoselective Approaches Using Aziridines and Epoxides

Sébastien Tardy^a, Joana Lobo Vicente^a, Arnaud Tatibouët*^a, Gilles Dujardin^b, Patrick Rollin^a
^a ICOA UMR 6005 CNRS, Université d’Orléans, 45067 Orléans, France
e-Mail: arnaud.tatibouet@univ-orleans.fr;
^b UCO2M UMR 6011 CNRS, Université du Maine, 72085 Le Mans, France

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Publication History

Received 30 April 2008
Publication Date:
05 September 2008 (online)

Abstract
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Abstract

d-glucose and d-fructose have been used as starting materials to prepare spiro-1,3-oxazolidine-2-thiones anchored on the third position of both carbohydrates. Following different approaches and depending on the carbohydrate template explored, stereoselective reactions have been developed via the formation of epoxides or aziridines.

Key words

azide - epoxide - spiro-compounds - chirality

References

1a Hultin PG. Earle MA. Sudarshan M. Tetrahedron 1997, 53: 14823

Google Scholar
1b Pellissier H. Tetrahedron 2007, 63: 3235

Google Scholar
1c Kunz H. Rück K. Angew. Chem., Int. Ed. Engl. 1993, 32: 336

Google Scholar
1d Dieguez M. Pamies O. Ruiz A. Diaz Y. Castillon S. Claver C. Coord. Chem. Rev. 2004, 248: 2165

Google Scholar
1e Boysen MMK. Chem. Eur. J. 2007, 13: 8648

Google Scholar
For selected recent publications, see:
2a Kim HJ. Kim Y. Choi ET. Lee MH. No ES. Park YS. Tetrahedron 2006, 62: 6303

Google Scholar
2b Kim HJ. Shin EK. Chang JY. Kim Y. Park YS. Tetrahedron Lett. 2005, 46: 4115

Google Scholar
2c Zimmer R. Orschel B. Scherer S. Reissig HU. Synthesis 2002, 1553

Google Scholar
3a Huang H. Chen H. Hu X. Baiand C. Zheng Z. Tetrahedron: Asymmetry 2003, 14: 297

Google Scholar
3b Burke C. Shi Y. Angew. Chem. Int. Ed. 2006, 45: 4475

Google Scholar
3c Kang J. Jho Lim G. Kyoon Yoon S. Yoo Kim M. J. Org. Chem. 1995, 60: 564

Google Scholar
3d Bach T. Höfer F. J. Org. Chem. 2001, 66: 3427

Google Scholar
3e Frohn M. Shi Y. Synthesis 2000, 1979

Google Scholar
4a Guz NR. Phillips AJ. Org. Lett. 2002, 4: 2253

Google Scholar
4b Zhang W. Carter RG. Yokochi AFT. J. Org. Chem. 2004, 69: 2569

Google Scholar
4c Jalce G. Seck M. Franck X. Hocquemiller R. Figadère B. J. Org. Chem. 2004, 69: 3240

Google Scholar
4d Chakraborty TK. Jayaprakash S. Laxman P. Tetrahedron 2001, 57: 9461

Google Scholar
4e Ortiz AK. Quintero L. Hernandez H. Maldonado S. Mendoza G. Bernes S. Tetrahedron Lett. 2003, 44: 1129

Google Scholar
4f Kinoshita H. Osamura T. Mizuno K. Kinoshita S. Iwamura T. Takahashi N. Iwamura T. Watanabe S.-I. Kataoka T. Muraoka O. Tanabe G. Tetrahedron Lett. 2005, 46: 7155

Google Scholar
4g Mendoza G. Hernandez H. Quintero L. Sosa-Rivadeneyra M. Bernes S. Sansinenea E. Ortiz A. Tetrahedron Lett. 2005, 46: 7867

Google Scholar
4h Kinoshita H. Osamura T. Mizuno K. Kinoshita S. Iwamura T. Watanabe S.-I. Kataoka T. Muraoka O. Tanabe G. Chem. Eur. J. 2006, 12: 3896

Google Scholar
4i Turconi J. Lebeau L. Paris J.-M. Mioskowski C. Tetrahedron Lett. 2006, 47: 121

Google Scholar
5a Crimmins MT. King BW. Tabet EA. Chaudhary K. J. Org. Chem. 2001, 66: 894

Google Scholar
5b Crimmins MT. McDougall PJ. Org. Lett. 2003, 5: 591

Google Scholar
5c Crimmins MT. Katz JD. Washburn DG. Allwein SP. McAtee LF. J. Am. Chem. Soc. 2002, 124: 5661

Google Scholar
For examples, see:
6a Saito Y. Zevaco TA. Agrofoglio LA. Tetrahedron 2002, 58: 9593

Google Scholar
6b Mio S. Kumagawa Y. Sugai S. Tetrahedron 1991, 47: 2133

Google Scholar
6c Guo J. Frost JW. J. Am. Chem. Soc. 2002, 124: 528

Google Scholar
7a Soler T. Bachki A. Falvello LR. Foubelo F. Yus M. Tetrahedron: Asymmetry 1998, 9: 3939

Google Scholar
7b Soler T. Bachki A. Falvello LR. Foubelo F. Yus M. Tetrahedron: Asymmetry 2000, 11: 493

Google Scholar
8 Maryanoff BE. Reitz AB. Nortey SO. Tetrahedron 1988, 44: 3093

Crossref Google Scholar
9a Lankin DC. Nugent ST. Rao SN. Carbohydr. Res. 1993, 244: 49

Google Scholar
9b Morin C. Ogier L. Tetrahedron: Asymmetry 2000, 11: 629

Google Scholar
10 Sahabuddin Sk. Ghosh R. Achari B. Mandal SB. Org. Biomol. Chem. 2006, 4: 551

Crossref PubMed Google Scholar
11a Garcia-Moreno MI. Diaz-Perez P. Benito JM. Ortiz-Mellet C. Defaye J. Garcia-Fernandez JM. Carbohydr. Res. 2002, 337: 2329

Google Scholar
11b Isoda T. Hayashi K. Tamai S. Kumagai T. Nagao Y. Chem. Pharm. Bull. 2006, 54: 1616

Google Scholar
11c Girniene J. Tardy S. Tatibouët A. Sackus A. Rollin P. Tetrahedron Lett. 2004, 45: 6443

Google Scholar
12a Alves RJ. Castillon S. Dessinges A. Herczegh P. Lopez JC. Lukacs G. Olesker A. Thang TT. J. Org. Chem. 1988, 53: 4616

Google Scholar
12b Kapferer P. Birault V. Poisson JF. Vasella A. Helv. Chim. Acta 2003, 86: 2210

Google Scholar
12c Bourgeois JM. Helv. Chim. Acta 1974, 57: 2553

Google Scholar
12d Bourgeois JM. Helv. Chim. Acta 1975, 58: 363

Google Scholar
12e Bourgeois JM. Helv. Chim. Acta 1976, 59: 2114

Google Scholar
13a Kapferer P. Birault V. Poisson J.-F. Vasella A. Helv. Chim. Acta 2003, 86: 2210

Google Scholar
13b Ahmadian M. Khare NK. Riordan JM. Klon AE. Borhani DW. Tetrahedron 2001, 57: 9899

Google Scholar
14a Fukuyama T. Jow CK. Cheung M. Tetrahedron Lett. 1995, 36: 6373

Google Scholar
14b Maligres PE. See MM. Askin D. Reider PJ. Tetrahedron Lett. 1997, 38: 5253

Google Scholar
14c Kroutil J. Karban J. Budesinsky M. Carbohydr. Res. 2003, 338: 2825

Google Scholar